title: Preparations of anthraquinone and naphthoquinone derivatives and their cytotoxic effects.
abstract: Chrysophanol and 1,8-di-O-hexylchrysophanol derivatives having nucleic acid bases at position 5 were synthesized. Furthermore, derivatives of menadione substituted at position 11 (type A naphthoquinone derivatives) or methylmenadione substituted at position 7 (type B naphthoquinone derivatives) modified with nucleic acid bases, amines and thiocyano, selenocyano or thioacetyl groups were synthesized. The cytotoxic effects of these derivatives on HCT 116 cells, which poorly express P-glycoprotein (P-gp), and Hep G2 cells, which stably express P-gp, were evaluated by performing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Results were compared with those obtained using 5-fluorouracil (5-FU), which has been used clinically. Several of these derivatives exhibited markedly higher potent cytotoxic effects not only on HCT cancer cells but also Hep G2 cancer cells as compared with 5-FU.
authors.affiliation: Faculty of Pharmaceutical Sciences, Josai University, Sakado, Saitama, Japan.
authors.forename: Xing-Ri
authors.initials: XR
authors.lastname: Cui
authors.forename: Ryota
authors.initials: R
authors.lastname: Saito
authors.forename: Takatsugu
authors.initials: T
authors.lastname: Kubo
authors.forename: Daijiro
authors.initials: D
authors.lastname: Kon
authors.forename: Yuich
authors.initials: Y
authors.lastname: Hirano
authors.forename: Setsuo
authors.initials: S
authors.lastname: Saito
mesh_terms: D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1 / Q000378:metabolism; D000880:Anthraquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D045744:Cell Line, Tumor; D005472:Fluorouracil / Q000633:toxicity; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D013329:Structure-Activity Relationship
chemical_list: D020168:ATP Binding Cassette Transporter, Subfamily B, Member 1; D000880:Anthraquinones; D009285:Naphthoquinones; D005472:Fluorouracil